Drunken Weaknesses
by jelanieandbedwardlover
Summary: Chuck and Jenny hang out one night and things move very fast. What could the outcome be to everyone around them? Inspired by the season 3 finale.
1. one night

**My first Gossip Girl fic ever! Whoo-hoo! Been wanting to do this for the past couple of weeks, inspired by Chuck and Jenny. The season finale tonight was my official inspiration (I wanted to change the ending too..*cries*)**

**So here we go…**

I woke up to a fast start. I knew the day was going to be horrible. My dad was mad at me. Lily was probably agreeing with him. Nate and Chuck were nice enough to take me in when my family was mad. I looked around the room, noticing I was still in Nate's bedroom.

_A week ago I would have rubbed this in Serena's face, _I thought, _not today._

"Morning," Nate cheerfully said, walking into his room, "Sleep good?"

I smiled, "Very. Thank you so much for letting me stay here last night. My dad wanted me to go back with Dan, but…I don't know. I don't think my family likes me too much right now."

Nate sat at the edge of the bed, "They love you," he replied while handing me a cup of coffee, "They're family. You'll get through this like everything else."

"Yeah," I sighed back. Nate's phone started buzzing and he went to check the caller id. "Serena?"

"No," he said, snapping the phone shut, "My grandfather. I better give him a call."

I nodded slowly as I walked out of the room. Yeah, Nate and Serena were having problems. But one of the things wrong was me. I tried to break them up and Nate was still unbelievably sweet to me. I didn't deserve it, or did I understand it.

There was a low chuckle from the doorway and at first, I thought Nate returned. When I looked up, I saw Chuck standing there with a huge smirk on his face.

"What's so funny?" I tried my best not to snap. He was, after all, letting me stay in his apartment.

"You and Nathaniel," he smiled wider, "I thought you were done helping me get my friend back."

"I am," I couldn't help it this time; I angrily replied, "Nate is my friend. You are my friend. You're both letting me crash. End of story."

He just nodded at first before replying, "Uh-huh," he kept at it. "Me and you are friends? Wow. I didn't know that." He just laughed again as he walked out of the room.

I threw a pillow where his path was. "Jerk," I muttered. _Why did Chuck Bass always make me smile? _

I got dressed fast and headed back to my dad's. Chuck couldn't make me smile. I was in love with Nate, that much was clear to me. But how come whenever I was within 20 feet of Chuck Bass, of all people, I felt instantly better? Like everything I was going through with my dad and Serena didn't matter?

_No, _I shook my head furiously, _Chuck is in love with Blair. _Blair hates me. Besides even if him making me smile meant anything at all, I could never do that. Even if we were mortal enemies, I could never steal a guy she loved.

Could I?

xxxxxxxxxxxxxxxxx

The day went fast. I got a text from Chuck at around 5pm. I flipped open my phone and read:

_Blair never showed at Empire State. Come hang out. We can watch New Moon._

Ugh. I knew ordering that last night would have some kind of comeback from him. He was joking of course, but I still hoped I could be like Bella and have two hot guys fighting over me.

Nate and…

Oh God. I wanted _Chuck _fight for me.

That was crazy. I sighed and texted him back.

_Sure. But anymore Twilight jokes and you lose a friend._

I smiled to myself as I hailed a taxi to take me to Chuck's apartment.

xxxxxxxxxx

"Chuck?"

I swung the door open and threw my purse down. Where was he?

"Chuck? Are you here?"

I heard footsteps coming from the kitchen. Chuck was wearing a t-shirt and jeans. I don't think I'd ever seen him dress so casual. He looked good. Why am I thinking like this?

"Hey," he smiled, "You're here." He sat on the couch and poured himself a drink then handed me a glass. "Want a drink?"

"Sure," I smiled, taking the glass from his hands as he poured the liquor into mine. "What are we doing?"

"Well, you gave me 24 hours New Moon on my pay per view, Humprey," he smiled, _What a gorgeous smile. _No, stop that. "So, I will now suffer 2 hours of vampires and werewolves. I'll probably be drunk anyways."

I laughed. "Well, get ready to be Team Edward, Bass," I smiled widely back.

xxxxxxx

"_This chick runs with vampires!"_

"_You can't really run with vampires. Cause they're fast."_

"_I know. But we're faster."_

I couldn't help but laugh at the werehumans. Chuck was actually watching the movie, but he seemed bored.

"This is what you watch?"

"Hey! I like what I like," I replied, "I can't imagine the types of movies you watch."

"I watch some interesting movies, okay?" He turned his head to me. We were inches from the others' face and I was a little tipsy right now.

"Yeah?"

He didn't answer. Chuck grabbed my face and kissed me. I kissed him back in an instant and it didn't take long before he grabbed me on top of him. I didn't know what to do. Kissing him felt so good. We were drunk and in love with other people.

But…

I didn't want to stop. I gripped his shoulders and he flipped me over on the couch and he was now hovering over me. There wasn't time to think. His hands were in my hair, on my arms and soon, he slid off my jacket. I didn't care. I grabbed a fistful of his t-shirt and pulled it over his head. It was only seconds our mouths were separated but it was enough to want him back on me.


	2. what just happened?

"Wait," I muttered as Chuck lifted me off the couch. The struggle was barely there. I knew we shouldn't, but I just _couldn't _stop kissing him. He carried me into the bedroom and laid me on the bed.

What were we doing?

"We can't," Chuck whispered as he pulled apart from me. "We've both have a few drinks and...we can't. We shouldn't." He was right. I knew he was right. Did I miss kissing him? Yes. Did I agree with him? No. But I also did at the same time.

"I know," I nodded, panting too much to say more than that. He sat up on the edge on the bed and I sat beside him.

Chuck nodded back, "I'm sorry." What was he sorry about? There are two of us in this. "I don't think I should have let it get this far."

He did? "No," I replied, "It wasn't just you. It was me too. I'm sorry." I tried my best to give him a sympathetic face. "You love Blair. It's not fair of me to take advantage of that."

"You didn't," he almost snapped, "I kissed you, Humprey, remember?"

"But I kissed you back."

"We shouldn't do this when we're drunk or impulsive," he stated, "Maybe when we're not wanting to be with someone else."

But I don't want to be with someone else.

I couldn't say that. Of course I couldn't. What would he think of me if I did? I decided to keep my lies as close to the truth as I could.

"Okay," I nodded again, "Agreed." But I couldn't help but think of how he suggested there _would _be another time.

_Mind out of the gutter, _I told myself, _he is the one who said it though._

He got up fast and held his hand out for me. I took it, happily and sweetly, as we walked back to the couch this all started on.

"Are we just gonna keep hanging out," I asked, "Pretend we didn't almost just do something?"

"That is exactly what we are going to do," Chuck smiled at me.

I chuckled at him as we watched the movie again. I didn't realize it got so far when we were…otherwise busy. Chuck put his arm around me when Edward and Bella were reunited. But it was in a friendly way. And we were friends. _Oh God, _I couldn't help but moan to myself. I wanna tell him I like him in a more than that way.

But this is Chuck Bass. He's in love with Blair. She could ruin me in a heartbeat. She has before. This would not end or start well.

xxxxxxxxx

The credits rolled as I looked over at Chuck. "What did you think?" I smiled at him.

"I don't understand how you like this," he sighed, "Or even pick a guy. One leaves the girl he claims to love and the other is kind of whiney."

I laughed so hard my eyes started to tear. "That's kind of true," I calmed a little, "But that's the fun part."

He glared at me, teasingly.

"This is nice," I murmured out loud.

"What is?" He was watching me with careful eyes.

"You, me, this," I motioned with my fingers to show between us, "I like us talking about things we like. I never expected that from you. No offense."

"None taken," he smiled, "Blair changed me a lot."

It was a whisper and I knew it hurt him to think of her not coming today. I had to be careful what I said with him, I needed to remember that much.

"I'm so sorry about--"

"Don't be," he cut me off.

That was the last of that conversation.

xxxxxxxxx

Chuck and me fell asleep on the couch. I opened my eyes at about 2am and looked around. _That all really happened, I almost had sex with Chuck Bass._

I started to stand up, struggling on my feet. Chuck was nowhere to be found. "Chuck?"

I heard a sound in the bedroom and he walked out. "I was gonna put you in there," he said, "I thought it'd be easier to sleep. I'll take the couch if you want."

"That's really nice," I smiled and tried again to walk. He came to my side and helped me walk. "Thanks."

He just nodded and helped me down when we got to the bed. "Night, Humprey," he smiled, "Maybe things will be normal between us in the morning."

"We've never been normal, Bass," I smiled back. "Night."

I was knocked out fast.

xxxxxxxxxx

The first thing I remember from the morning was knocking. "Jenny?"

"Yeah?"

"I ordered room service," he replied, "if you want some breakfast, it should be coming soon."

"Okay, thanks," I said back as I sat up on the side of the bed.

There was a knocking at the door, but it wasn't the bedroom door. I assumed it was the food and stood up. Then I heard Chuck.

"Blair?"


	3. Getting it out

**A/N: Thank you to my subbers and my other readers for the patience. I know I get a little slow with my updates so here is chapter three *smiles***

BLAIR? What the hell is Blair doing here? She can't be here. She broke Chuck's heart today. It was a good day, we were getting along. Now he's going to tell me to leave when the front door is passable and Blair will stay.

Why did I get myself into this? I quickly hid out of site in Chuck's bathroom because it was the closest room to where I was standing. I listened for more.

"I went," Blair started, "I went to meet you today. I didn't want to. All my instincts told me not to, but then Darota went into labor. It was amazing and I started thinking. I was too late, though." She smiled at the end as she held her two hands in the front to reveal a beautiful pink bouquet of flowers.

I had to get out of here.

"Say something, Chuck," she pleaded with him.

He looked around, nervous, confused…conflicted. Why was he conflicted? Here was Blair, what he was waiting for, on his doorstep.

"You should go," he whispered.

"What?" Blair asked.

"You should leave, Blair."

"Why? I came, Chuck," she almost begged, "I went to the Empire State Building today. I was late because I had to be there for Darota. I brought your flowers. Chuck, it means something."

He sighed, "Look, I waited for you, for a long time. Now you come here, my flowers in hand and say 'I didn't want to come but I thought about it'? No. I think you should leave."

"Chuck – "

"Please, Blair," it was his turn to plead. I could imagine the sadness in his eyes when he said this. "Please, give me some time, okay?"

Blair nodded, about to cry it looked like, "Okay. Good-bye, Chuck." She turned back out and he shut the door behind her.

"Jenny?" he called when Blair was officially gone. "Are you still here?"

"Yeah," I said, sneaking out of the bathroom. "I'm sorry I was here for that."

"Yeah, well, I'm sorry you had to be here for it too," he sighed. " What do you want to do now?"

Huh? "You still want to hang out?" I questioned, "After Blair came and…everything else?"

"Jenny," Chuck walked over to me and put his hands on my shoulders, "I like spending time with you. Blair was bad timing and I didn't want to see her right now."

He liked spending time with me? Over Blair? Did he feel like I did? Maybe just a little bit?

"Okay," I tried not to smile. "What should we do? Cause I think drinking was a bad idea considering what happened last time."

"That wasn't a bad idea," he grinned at me.

"You trying to seduce me, Bass?" I smirked back at him.

"Only if I can," he gave me the sexiest smirk I'd ever seen.

I laughed to myself. "I think you had enough to drink tonight, don't you?"

He laughed with me.

"Fine," he sighed, "I got some work for the hotel to do. You can keep me company to make sure I don't fuck up my money, okay, Humprey?"

"Deal," I smiled.

xxxxxxxxx

It was hours later. Chuck had been going over accounts and portfolios like crazy. I had never seen him like that before. A hard-working, responsible Chuck Bass. It wasn't exactly helping my situation of liking him.

It was getting much worse.

Every now and then, he would look at me. I would smile and he would then he'd get back to his papers. God, I was falling for Chuck Bass. Who would have thought?

"Do you need to go home?" Chuck asked me out of the blue. Did I? My dad was mad at me and I stayed here sometimes.

I shook my head, "No, not tonight." I gave him my best devious smile and he gave me one back.

"Do you want to stay in Nate's room or mine?"

"Would Nate want - "

"Mine it is," he cut me off.

Chuck led me to his room and turned on the light.

"Do you want to borrow clothes?" He asked. He sounded awkward. That was a first.

"Um…" I looked down at my dress. "Yes?"

He just nodded and went to the dresser closest to the window. He pulled out a t-shirt and sweatpants.

"Wow," I gasped, "Chuck Bass owns sweatpants, who knew?"

He laughed, "You do. Don't tell anyone my secret."

"It's safe with me," I smiled as I walked back into the bathroom to change. Chuck must have been getting clothes out for himself since he was sleeping on the couch tonight. I felt bad because it was usually Nate I did this to.

I walked back out and Chuck was placing pillows on the couch. "Okay," I sighed, "I think I'm just gonna crash. It's late."

"It is," he answered when I yawned. I tried to stop it but it happened anyways. Damn reflexes. "Good night."

He just nodded. I went back into his bedroom but grabbed my phone first. As soon as I was in the bed, I looked through my contacts and found the person I wanted to text.

_I'm sorry I've been such a bitch lately. But I need to talk to u. Plz._

Send.

A few minutes later, my phone lit.

_What is it? R u okay?_

I typed another response

_Yes and no. Meet me 4 bfast?_

It took a bit longer this time. But the text came.

_Sure. Come by my mom's._

I could hear the sigh in her words as if she had really said them. I shut the lights and places my phone on the table and went to sleep.

xxxxxx

When I woke up in the morning, Chuck was gone. All evidence that he even stayed on the couch was gone and he left my clothes outside the door on a hanger. How sweet. I quickly went in the shower and changed, then was out the door.

It felt longer than I remembered to get to this familiar place. I went in the elevator and the stairs until I found the right room.

She was there, waiting.

"Hey, Jenny," she said as I entered.

"Hi, Serena," I tried to smile back at her. I was horrible to her and Nate. But I needed my friend. Who was also friends with Blair. "I need to talk to you."

"About what?" she replied. She was still mad.

"First," I sighed, "I'm sorry about everything. About Nate, being such a bitch to you, trying to ruin your relationship, getting involved with your mom and my dad's relationship. I had no right to get in the middle of any of that. I feel so horrible, Serena."

"I know," she sighed, "I forgive you. It's not like I've never been a bitch to you or anyone else before."

"Thank you," I sighed in relief. I was glad to have my friend back. "I need to tell you something. Something I didn't expect at all. Or want."

"What is it?"

"I think I'm falling for Chuck."

There. I said it.

"WHAT?" she screamed, but regained her calm, "Chuck? As in Chuck Bass? As in Blair's ex boyfriend?"

"Yes," I nodded, "Look, I didn't even realize it at first. We've been hanging out a lot lately. And I guess my friendship with Nate made me see a different side of him. And I don't know, Serena."

"Wow," she mouthed, "that is big."

"There's more."

Her eyes widened, as if there could be more.

"We almost had sex."

**A/N: Thoughts? Leave a review.**


	4. Bass Confessions

**A/N: I am so so sorry I have been horrible at updating this. I will try to get back to my regular writing times but here is chapter 4. FINALLY.**

Watching Serena's eyes bulge out of their sockets was not what I was thinking of when I blurted out what almost happened.

_"We almost had sex."_

Did I really just admit that?

"What?" Serena screamed at me. Her face was angry and confised. "Did I just hear that? You almost slept with _Chuck Bass_? After everything with Damien and how me and Nate tried to get you to want your first time special, _that_ almost happens? Explain this."

I took a deep breath and started, "Chuck and I have been hanging out a lot lately since him and Blair broke up. So we were watching New Moon last night and we kissed. And we did go into his room…but it wasn't right for us to be doing that."

I sighed. How would she take this? At first, she just stared at me, watching me carefully, as if she thought I'd slip and that was a lie.

"Seriously?"

"Yeah," I nodded.

Serena sighed now. "What the hell were you thinking?" she exclaimed as she hit my shoulder. "It's CHUCK!"

"I know, I know," I answered, "but there's a sweet side to him, Serena. I never knew it was there til a few weeks ago."

"Chuck has a sweet side," she whispered to herself, "Who would have known?"

Me. Blair. Lily. The only ones he showed that side to.

"Jenny," she sighed, "Are you covering from him?"

"What do you mean?" The question baffled me. Why would I cover for him? The only other times I really had encounters almost like this was at the Kiss…_Oh. _"No. No! God, no. Are you thinking he tried to rape me or something?"

Serena shook her head, "No, of course not. But 2 years ago, he was a good liar that he got you on that roof with him. Maybe he did it again because he missed Blair so much."

"Do you think I would defend him if he tried that again?" I gave her a curious look and she smiled. "No, Serena, I would _never _let Chuck, or anyone for that matter get away with that. I did text Dan in the first place because I needed him, remember?"

"Yeah," she sighed. "How is Dan?"

I shrugged. "I don't know. I haven't exactly talked to him yet in a few days. Why? Have you heard from him?"

"I was just wondering," she smiled again.

Then it clicked.

"Serena…" I accused, "Are you falling for my brother again?"

"No!" she answered too quick. "No," she calmed down a little. "I'm not. I'm with Nate. You know that, Jenny."

"Yeah, but even if you're with someone, you can have feelings for someone else."

"I know," she replied, "But it's not that." She sat down on the couch and sighed. "I have to confess too. Me and Dan have been hanging out a lot, too. And I don't know…all those feelings from those 2 years are flooding back to me."

"It's okay to want to be with him," I said back. How else could I answer?

"I know that, too," she whispered in a small voice. "Just like how if you really do have feelings for Chuck, you should do something about it."

I shook my head. "I couldn't. He loves Blair. She hates me. Imagine if something happened with me and him? She'd destroy me."

I sat down next to Serena and she stared me right in the face. "Jenny," she sighed, "Blair loves Chuck. So much." Thanks for that reminder. "And he loves her. And when you love someone so much, you want them happy. You love them so much that it's possible to let them go when there is something out there that they want insanly and irrationally. I think what Chuck wants right now…is to be with you."

No. That wasn't possible. There was no way that a few days would pass and Chuck would suddenly want me.

"No, he doesn't."

"Okay, fine. I won't say anymore," she relaxed onto the couch. "But thank you for telling me. I'm glad after all the crap we've been through lately, and even with Blair being my best friend, we can tell each other things like that."

"Me, too," I smiled. I leaned back onto the couch too and sighed.

"Jenny?"

"Yeah?"

"Chuck really watched New Moon?"

I nodded my head and we both starting laughing.

xxxxxx

I walked into my dad's loft and sat down at the kitchen countertop. What a day. What a fricking day. First last night with Chuck. Then me and Serena made up. Now I get the whole place to myself. Now I can just think. Then the door opened.

"Hey, Jenny," Dan said as he walked in. "Where were you last night?"

Uh-oh.

"A friend's," I shrugged. Like I could tell him I was at Chuck's.

"Oh," he shrugged back. "You could have called, you know. Us in your family like knowing you're okay."

"Oh, sorry," I tried to smile, "I was watching a movie and I fell asleep. By the time I woke up again, it wasn't exactly a time to call you or Dad. Sorry I made you worry or anything."

"It's fine," he answered.

"I saw Serena today." He stopped his way to the fridge and froze for a second then started again.

"Yeah? That's good."

"It is," I smiled. I knew he'd be thinking of the same things she was. He was never meant for Vanessa anyways. My brother would always love Serena Van Der Woodsen.

**A/N: I know, no Chuck. I'm sorry about that. I wanted Jenny's thoughts on this and what happens when she told Serena. My Serena is nicer. I'm not her biggest fan lately so I'm fixing that friendship. Haha. Review if you want.**


	5. Simple as That

**A/N: Chuck's POV**

What was that last night? And with Jenny Humphrey? The girl I tried to use after the Kiss on the Lips party almost 3 years ago? What was I thinking?

To be honest, I don't know.

Over the last few weeks, me and Jenny have become closer. I might even say friends. Nate was helping her through a tough time with her dad and here she came. After my break-up with Blair, I thought nothing mattered. Blair was the first girl I ever really loved. I didn't think I could be good for her anymore so I resorted to my old self.

My old self would have taken Jenny to his bedroom weeks ago. This me wouldn't. But last night…how do I explain what almost happened? I'm not a over-thinker and I certainly don't worry about things like how the girl I almost hooked up with feels. I just focused on what I was doing and when it was done, it was done.

But this was different.

This was the new me.

This was Jenny Humphrey.

A girl I first met when she was a freshmen and now she's become this major, almost adult with a mind of her own and the kind of potential to be Queen at the school. Jenny wasn't so little anymore, as Blair has always called her Little J. She's not that same girl anymore.

As I paced around my apartment, looking at my bedroom where Jenny stayed last night, I replayed it all. Why the hell did I watch New Moon? Oh yeah. She rented it while Nate snored the night away. I have to admit, that part made me laugh. But how did we go from watching a movie to almost having sex? It's like it came out of nowhere.

But it didn't.

I knew what I was feeling. I _liked _Jenny Humphrey. And I don't just mean like. I really _like liked _her. What the hell has gotten into me? I'm Chuck Bass. I don't fall in love. Yet I fell in love with Blair and that crumpled. And she showed up last night while Jenny was in the other room. I can't imagine what she was thinking. I didn't expect Blair to come over, or even come to the Empire State Building yesterday.

But she did. And she was too late. Not just because I was gone but because I realize I have feelings for Jenny.

Hpmh. Chuck Bass have feelings for a girl. It sounds so cliché.

But here I sit, thinking about her and wondering what she's doing. Exactly what a guy in love would be doing. I wasn't insane though. I don't think I'm in love with her. I just enjoyed spending time with her and we had fun. It may have been me being shirtless and almost being Jenny's first time, but we still had fun.

I saw her smile. Jenny doesn't smile much lately. But she did with me. I wonder why that is. She liked Nate. How come she didn't smile more for him?

It was all bugging me.

My sudden feelings, although they weren't so sudden when I knew there was something about Jenny the first time I saw her those three years ago. She was amazing and I ruined that. So I became a better man. I apologized. We became friends. And now I'm the guy who makes her smile.

I don't know what to make of that. I don't know what to make of any of this.

Me and Jenny, it couldn't happen. It shouldn't.

Yet there was something in me that really wanted to be with her.

I walked into my bedroom where she slept last night and noticed she made the bed. It was the first time I came in here all day, in fear of what it might remind me almost happened. Now in fear of what I want happen.

What did I want happen?

I wanted to think I wasn't crazy. I wanted to know she could feel the same, or laugh me off so I could go back to how it was.

But I couldn't.

I wouldn't.

I had to face this. I had feelings for Jenny. Simple as that.


	6. Laying it out

Jenny's POV

I walked into the loft with an exhausted sigh. I didn't want to go home, that was for sure. But I knew I couldn't just go to Serena again, she is best friends with Blair. Diving more into my feelings for Chuck could get out that way.

I needed to think. So I grabbed a soda from the fridge and sat down on the sofa. Chuck was my friend. I almost slept with my friend. Maybe I should analyze it that way. I couldn't start sleeping with my friends. That wouldn't be right. But…he wasn't just a friend. He was kind of a confidante to me now.

As strange as it seems, I think I'm his too now.

I sat there in my own thoughts for a couple of minutes it seemed like when there was a knock on the loft door. Who would be coming here? I stood up anyway and opened the door.

Crap.

"Hey," he said.

"Hey," I whispered, "What are you doing here, Chuck?"

"Can I come in first," he asked. I nodded and he made his way past me. "I thought we should talk, Humphrey. Last night was…well, it was a hell of a surprise."

I took a deep breathe and sat on the couch and he sat beside me. "Yeah," I replied, "It definitely was that. But, you know, I'm not going to tell you that you have to apologize or anything. It's not it was all you so I guess - -"

"Humphrey," he cut me off, "Let me talk for a minute, okay?" I nodded. "Last night was a surprise..in a good way. You surprised me. I know this is something you expect to hear out of Chuck Bass' mouth but this last year, I've really grown up and I've changed. I know feelings when I have them and I sure as fuck wasn't going to let them pass when I feel like I do with you. Maybe I'm turning into a wuss or something, but I needed you to know that."

I didn't think. I kissed him. I kissed him intensely and fiercely. Like I never kissed anyone before. He kissed me back with the same passion I felt inside me. It sounds lame to be thinking like this but it was how this felt. Chuck made me feel different.

But we shouldn't be doing this. I pulled away almost as fast I pulled forward. Chuck's eyes were still closed and he obviously didn't expect me to kiss him or to pull away.

"What was that," he asked me.

I tried to smile, "I don't know."

"Do you -" He started, "Do you feel the same?"

It felt like one of those things where you had to confess something right before you die, like I was confessing one of my biggest secrets by answering that one question.

First, I took a deep breathe then sighed, "Yes."

"Wow," he whispered, "Who would have thought this? I mean, a few months ago, it seemed like we were enemies and now here we are, sitting in your dad's loft, confessing our feelings. It's kinda crazy."

"Yeah, it is," I laughed. "So, what do we do now?"

Honestly, I wanted to be with Chuck. I wanted to see where this went. I wanted to be able to kiss him on a daily basis and not be afraid of what other will think. I knew that was an unreasonable thought, but I wanted it bad.

"I don't know," he replied back to me. "Let's take it one day at a time and see where it leads us. Maybe not exactly be in a relationship right away or publicize this but, we could try to see how we feel. Could I be any more different that I usually am?"

"I don't think so," I laughed, "But I like it. You've grown up, Bass."

XXXXXXXXXX

Chuck's POV

Did that really just happen? Did I just spill my feelings for Humphrey out to her? I really am a changed man. I don't screw girls on a daily basis anymore. I don't go to as many strip clubs as I did. You can tell that Blair matured me. Being a relationship made me into a new man. Maybe not someone who will play house and give up drinking and a good time but a changed man.

I liked Jenny Humphrey. I was falling for her. She said she felt the same way. She kissed me when I said all that. And I kissed her back.

I'll be honest, this scared the shit out of me. I was only in one real relationship before and I don't think Jenny's had a great time in that department either. Considering her last boyfriend was a drug dealer who tried to sleep with her, I don't think that's the best history.

But me and her – we could be different. If someone would have asked me a few years ago, hell, a few weeks ago, where I think I'd be right now, it would not have been here. I thought I'd be with Blair. There was no denying I did still love her. New feelings didn't change that. But they were there. I knew I'd have to tell Jenny about them being there. Maybe I wouldn't have to. I knew how she felt about Nate and neither of us talked about it.

It could be implied.

Watching Jenny get up to get me a soda was a nice gesture. I smiled when I realized she knew I wanted a drink without asking. I should've known there wasn't any alcohol lingering around.

She sat back down and handed me the drink. "If you want something else, I can get you it," she said.

"No, it's fine," I answered her back. "I can drink a soda, you know."

"No, I know," she almost sounded nervous, "I was just wondering."

I chuckled to myself over her almost stutter. "I'm fine, Humphrey."

"Ok," she whispered.

Yeah, I was definitely screwed now.


	7. Planning the first date

**A/N: This is LONG delayed, I know. Life got in the way, I was stumped on how to make a great chapter. **

**This is for everyone who stuck around, waited for updates, reviewed, read and recommended. Most of all, it's for Dana, my Chuck and Jenny weatherwomen who predicts we're gonna get some good scenes next season.**

**Enjoy **

The days that went by were a blur. Chuck kissed me again. Chuck told me he had feelings for me. We were dating. Sort of. I don't know exactly what we are or what we're doing but I do know is I can't control what I feel right now and he feels the same way.

If someone told me a year ago even that I would be standing here, thinking about Chuck Bass and having these feelings, I'd tell them they were insane. But here I am.

After our confessions that day, we sat and watched tv. We relaxed. I felt the most comfortable I have in a while sitting on the couch with Chuck. The thought of it all made me smile. When he went to leave, he kissed my hand like a gentlemen would and told me he wasn't going to suddenly change his mind about all of this.

I was about to go back into my room so nobody would notice my good mood, but my cell phone buzzed. The name "Chuck" came up.

_Hi._

I smiled. He was texting me a "Hi".

_Hi yourself._

_What r u doing?_

_I'm at home. What about you?_

Nothing. Why didn't he text me back? Then there was a knocking at my door. Who the hell was it?

I walked slowly to the door, opening it to see a guy holding a envelope.

"Are you Jenny Humprey," he asked me.

I nodded, "Yes." He handed me the envelope and I was still confused. "What is this?"

"I was asked to personally deliver that to you, Miss Humprey," he replied, "Chuck wanted me to make sure only you received it."

Chuck. _Oh._ Is it why he didn't text me back?

"Okay," I managed to get out, "Thank you." The man just nodded and then left. What did Chuck write to me that he couldn't text and no one else could see? Slowly I opened the flap and read the page. It was an invitation.

**Jenny – **

**You are invited to an extravagant night. Meet me at my lobby tonight at 8 pm.**

**- Chuck **

He wanted to have dinner with me. There was no moment that I felt as much of a girl as I do as that moment. I needed to go shopping and make myself a mental note to try not to show how excited I am. I grabbed my bag and rushed out the door.

xxxxxx

Why was it so difficult to shop for a date? Arrgh. Just in my middle of my pre-date jitters, I slammed into someone. I looked at who it was and wished I was back home.

"Blair."

"Little J."

"How are you," I had no clue what to say to her.

"How am I," she questioned, "Well, I know you know of me and Chuck's break-up. And I bet you wanna rub it in my face. So go ahead. Get it over with."

"I don't want to do that," I whispered. I doubt she even heard me.

She did. "What did you say?"

Clearing my thought might help. "I said...I'm not going to rub it in your face about the break-up. I know you really loved Chuck so I'm staying away from that."

"Huh," she said. Not like a question, but just when someone's shocked. "Wow. So no mocking, no laughing, no saying no one will ever love me? I guess I was right. You aren't mature enough to handle being the Queen."

"You're wrong," I snapped, "I can handle it. Just because I'm not being a bitch doesn't mean I can't get the job done."

"It does, actually," she smiled, "Being queen is being a bitch. Really, let's be honest here, Humprey. It is all about being a bitch. Denying that won't change it." I tried to open my mouth to say something but my phone buzzed again. Being clumsy, I dropped it and Blair picked it up. _Oh, shit._ "Why is Chuck texting you?"

It wasn't an accusation. It wasn't even nosy. She seemed hurt. "We're friends," I said, "we talk and hang out. Why? Do you think I'm gonna do dirty work for you?"

Her eyes looked like she didn't know why that thought crossed my mind. "No," she shook her head, "How is he?"

Huh? "How is he," I stuttered. "Um…he's good. He told me you didn't show up to meet him."

That caught her off-guard. "He did? I went, though," she tried to smile, "He was gone and his flowers were in the trash. I missed him by who knows how long."

I remembered her coming at Chuck's door that night while I waited.

"He doesn't want me back, you know," she continued. "I thought he did but I guess it really is over now." What could I do right now to make this right? "Will you tell him I miss him?"

"Um…," what was I supposed to say? "It's not place to get involved."

She sighed. "You know what? I shouldn't have asked you. I shouldn't even be talking to you about this. Just forget this ever happened, all right?"

I nodded and she backed away. What just happened?

Blair wanted Chuck. He turned her away. For some reason, he wanted me. But why? It confused the hell out of me. But I wnet and finished my shopping anyway.

xxxxxx

8pm

Getting out was easy. What I was about to do was hard.

Walking up to Chuck in his building's lobby in my new skirt gave me confidence. I was not the same girl I was years ago. I could do this.

A smile crept on his face when he saw me. "Hey."

I smiled back. I couldn't help it. "Hi."

"Should we get going?"

"Um, Chuck, wait," I grabbed his arm as he turned to the doors. "I need to tell you something." He nodded for me to continue, but it was obvious he had no idea why I was hesitating. "I ran into Blair today."

He froze.

"I can't do this, Chuck," I said just above a whisper, "She wants to be with you. I can't just take this chance with you. I'm sorry."

I walked to the door, without turning back.

"Jenny! Wait!" I could hear him starting to follow me so I ran faster.

I wasn't going to be with him while Blair wanted him. There was too much at stake. I jumped into the first cab I saw.


	8. The Search

**Author's Note: This chapter is gonna be switching POV's from Jenny and Chuck : )**

Chuck POV

What just happened? One second we were going on a date, which everyone knows I don't just do with anyone. The next, Jenny's running out of here telling me Blair wants me back. This is one fucked up situation.

I walked out into the street and tried to find her, or a trace of her. Nothing. There were some couples walking around and other people but no Jenny.

Where did she go?

xxxxxx

Jenny POV

Sitting in this cab felt like forever. It was only 10 minutes since I walked out that door from Chuck. Ten minutes since I left what my heart wanted and ran out. Ten minutes since I tried to fix Blair Wardolf's relationship.

What was wrong with me?

Rethinking seeing Blair this afternoon, the past few days and running away from Chuck was getting to me. It all happened so fast, it seemed. First the feelings, then the confessions now I was going to lose it all.

Blair was right.

I can't handle Queen. What kind of Queen runs out on a chance to be with a great guy and a way to get under the former Queen's skin and what do I do? I ran away into the first club I saw. Chuck shouldn't waste his time on me. I'm nothing but a wannabe, that 14 year old girl following after Blair and Serena, trying to fit in.

Maybe this was never my world.

Dan was right. Everyone was right. The first tears start falling down my face and I try to sniffle them in. The driver looks back at me through the mirror and sighs. I know he's not used to teenagers crying in his backseat. What is wrong with me? And how many times am I asking myself that same question since I left the hotel?

"This the place, miss," the cab driver asked me.

I nod, "Thank you," and hand him the money. He smiles and I try to return one with my own and I climb out of the cab. The car drives away and I'm standing there, in front of a giant neon sign. I sigh one deep breath and walk in.

xxxxxx

Chuck POV

I banged on the door as loudly as I can. _Come on, _I thought to myself. Suddenly the door swung open and I was looking at a very surprised Lily.

"Charles," she smiled, " What are you doing here? And what's so urgent?"

"Is Jenny here," I spit out. She looked at me with questioned eyes and sighed. She wanted to an explanation. "I was meeting up with her, she seemed upset and ran off. I was worried about her."

She motioned for me to come in. "Sit down and tell me what's going on," she sighed, "I didn't know you and Jenny were hanging out."

Now I sighed. "We're...we're starting to…I don't know how to say this any way to make it sound good." Lily narrowed her eyes at me. Why did she have to know me so well? "I like Jenny. In more than a friend way and we were gonna try to go on a date or see what it's like to be out together but she was upset because she saw Blair and left" I huffed out without a breath. I stared at Lily while she processed what I told her and she knows I'm not the type to tell parents, especially a girl I like's step-mother what's going on.

"Well," she started, "that is big." She seemed to process a little bit more then started on. "How did this happen, Charles?"

"I don't know," I answered honestly. "One minute I was laughing at her crappy taste in movies, the next we kissed and now we admitted feelings. Lily, you know me. You know I don't admit feelings."

"I'm gonna try calling her cell," she stood up and walked to the island in the kitchen.

"I tried that."

"But I'm not you," she smiled. "Maybe Jenny is embarssed and just not talking to you at the moment." She began dialing the phone and I watched her intently as she slid the phone to her ear. Then she frowned. "Voicemail" she mouthed at me. "Hi, Jenny. It's Lily. I just wanted to check on you, see how you are. Listen, call me when you get this, okay? Thanks. I'll talk to you later." And she hung up.

"You didn't mention me."

"I didn't want to let her know you came to me."

"Thanks, Lily."

xxxxxx

I walked into the huge entrance I was so used to. My eyes scanned over where so many things happened and so many things were left unsaid.

"Chuck?"

My head snapped up to the top of the staircase. Blair was looking down at me with surprise and relief all in one look. "Blair," I nodded toward her as she begun walking down the steps.

"What are you doing here?"

She smiled, genuinely interested. "Jenny told me you were talking to her today." Her smile fell as fast as it appeared. "I know bits but can you tell me what happened?"

"I knew Humprey couldn't keep a secret," Blair spat, "I told her to forget about it and here you are, after she told you. Did she say I'm desperate? What?"

I shook my head. "No," I half-smiled. "She told me you wanted me back." She sighed. A breath of relief and happiness. Maybe she was even grateful to Jenny. "Is that true?"

Blair looked straight into my eyes and nodded. "I'm so, so sorry, Chuck," she apologized. "I didn't mean to spill that all out, especially to Jenny Humprey, of all people. But I saw your name on her phone and…I don't know. I miss you and I know you said no. But I wasn't trying to do anything to change your mind."

"Wow," I whisped. "That's gotta be one of the most honest things I've ever heard you say, Blair." She laughed a little laugh. "Going soft, Waldorf?"

"Never, Bass," she smiled, "But…are you?" He question took me off guard. "What were you doing hanging out with Little J? What made you two such good friends, huh?"

"It's nothing," I lied. I couldn't tell her. Being here with her…knowing she still wanted to be with me after I pushed her away again, was getting to me. "Blair…"

I didn't have time to think. I leaned in and kissed her. It turned into more than a peck and more than it should have been when my phone buzzed. I broke apart from Blair and searched my pockets for my phone.

"Oh my god," she worried, "What are we doing? What am I doing?"

"Blair…" and I found my phone. Lily's name lit up the screen. "Yeah?" I answered. What she told me caused me to nearly drop the phone when I hung up.

"Chuck," Blair's voice was suddenly closer. "Who was that?" I didn't answer. "What's wrong?"

"It's Jenny," I finally replied, "Lily wanted to tell me where she ran off to tonight after she told me about seeing you."

"Well, where was she," she asked, confused and interested.

"Downtown…at a sleezy bar."

xxxxx

**What happened down there? Who found Jenny? All coming soon.**


	9. Guilt Trips & Family

**Author's Note: I'm gonna drop the POV's for a chapter. Maybe if I write better without it then I'll keep it up.**

**And thank you for all the reviews! I honestly don't know what to respond with. Thanks for taking the time to give me your thoughts and I am going with the flow. The story and characters will take me where they want to take me, I guess. Haha.**

_"Chuck," Blair's voice was suddenly closer. "Who was that?" I didn't answer. "What's wrong?"_

_"It's Jenny," I finally replied, "Lily wanted to tell me where she ran off to tonight after she told me about seeing you."_

_"Well, where was she," she asked, confused and interested._

_"Downtown…at a sleezy bar."_

Chuck dropped the phone in the instant he hung up. Blair followed behind him as he raced out to the elevator.

"Where was she, exactly," Blair questioned Chuck as the doors closed and he pressed down the buttons to go to the first floor. "What about her dad? Dan? Shouldn't they be taking care of this?" Chuck just stared at her. He didn't know if they even knew. But surely, if Lily called him, she would tell everyone else or at least someone in the family.

"I don't know," he finally answered. "All I know is Jenny's in a trouble so someone needs to get down there and check it out."

The elevator finally started moving and they were at the entrance so fast that Chuck was racing the door. "Wait! We need a cab," Blair screamed. Chuck stopped and noticed there were barely any cars on the street. How were they going to find a cab? "I'll call for one, if you want," she whispered but loud enough for him to hear.

Chuck looked at her questionably, "You're coming?"

She nodded, "We may not be together and me and Jenny may not be the best of friends in the world but you know what? You care about her. You care enough to run out of my apartment for her and if that's true, then something that hurts you is not good. So, yes, I'm coming. Do you not want me to?"

Chuck thought about for a second. Coming to get Jenny with Blair by his side might not be what she'd want. But it was all he had. He doubted Lily could get there or that Dan or Rufus would even be able to get there fast. He had no idea where they were. So he looked back to his ex-girlfriend and came up with a decision. "No, it's fine," he answered back, "Can you call for that cab?"

"Sure," she half-smiled, as she picked up her phone and began dialing.

xxxxxxxxxxx

Serena was in shock. Her mom just hung up with her and told her what was going on with Jenny tonight. What should she do? She knew she had to call Dan. Or Nate and Vanessa. Someone. She quickly dialed Dan's number first and waited a few rings til he picked up.

"Yeah," Dan said as the greeting.

"Hey, Dan," Serena talked into the phone, "Listen, my mom just called me and told me Jenny was at some bar downtown. I didn't know what to do or if you knew…"

Dan froze. "What," he almost screamed, "Was she with anybody? What could make her go there?"

She just shook her hand. "I don't know. I know she had plans tonight with Chuck -"

"Chuck?", he sputtered. "What was she doing with Chuck?"

Crap, she thought. "Right," she tried to cover up, "You didn't know."

"Know what," he asked, "Tell me. This is about my sister, Serena."

"Jenny likes Chuck," she replied, "And they've been hanging out for a while. They're friends."

Dan sighed, "How come I didn't know this?"

Serena shrugged but he couldn't see that, "I don't know," she whispered again. "Look, let's go check it out, see if your sister's still there. Ok, Dan?"

He sighed again. "Meet me outside your place. I'm coming there."

xxxxxxx

Jenny sat on the bar stool impatiently. Lily was talking to the bar owner. Well talking was putting it nicely. She was yelling at how the club serves to underage girls. Jenny just sighed, she didn't see it as a bad thing that she was here, or that she was drinking. It was all a way to escape a failed relationship. Of course it would have had to start in order to be called one.

Lily screamed louder, "But she didn't have ID! How could your bartenders just serve a girl without checking her ID? Do you think she looks old enough? No, better, does 'looking' a certain age mean they must be?" Jenny tried to zone out the conversation again. All she really wanted right now was to go to sleep and for Lily not to call her dad. At least she knew one of the above was happening.

Suddenly, Lily was walking towards where Jenny sit. "I called a few people," she sighed.

"No -"

"Listen," Lily started, "It wasn't your father. I told Dan." Jenny breathed a sigh of relief. "And Chuck." _What_, Jenny thought. "Now, wait, before you say anything, Chuck came over to see you before I knew where you were. I thought he might be interested in knowing where I found you."

"Can I just go home," Jenny whispered. Her eyelids were starting to close and she felt the alcohol rise in her throat. Her thoughts raced to the guy she was dancing with when Lily found her and she smiled to herself. She wanted to move on and she was having a good time. If only Lily didn't come….

"Ok," her step mother sighed. "But, what if they come? You and me should wait here. And then later, we're gonna have a talk about meeting strangers in bars."

"Fine," she grumpily answered. It seemed all at once when they saw Dan and Serena walk in. "Crap," she whispered to herself.

"Jenny!" Dan almost screamed. "What the hell are you doing here? Are you crazy?"

"Dan," Serena tried to calm him down. "Are you okay, Jenny?"

Jenny nodded, "Yes." All she wanted to do was go home and the possibility that Chuck was coming was not going over well with her heart. "Can we please go now? I'm really tired." Serena just nodded and helped Jenny off the stool. When they were getting closer to the door, Jenny turned to Lily. "Are you going to tell my dad?"

Lily was thoughtful for a moment. "No," she answered. "I guess it all depends on you. I could tell him and have him punish you, or you can tell him yourself." She just nodded back to her stepmom and continued walking. Before she could get any further, there was Chuck in the doorway…with Blair.


	10. Faceoff

_She just nodded back to her stepmom and continued walking. Before she could get any further, there was Chuck in the doorway…with Blair._

"Jenny," Chuck said the second he saw her. "Are you okay?"

"Yeah," she tried to smile and be upbeat even though it was killing her, "I'm fine. We're leaving." Jenny tried to pull Serena along with her to leave sooner but Chuck stopped them. "What?"

"What the hell were you doing here?" Chuck fumed at her, "You run out and then come here? Of all places, you land in a bar?"

"Please, let me just go home," she pleaded. Chuck saw the pain in her eyes and just nodded. Jenny and Serena walked through as Blair and Chuck moved aside for them. Dan got right to their place.

"Chuck."

"What, Humphrey?"

"You and Jenny?," Dan asked him. His face showed he had no clue that was happening. "Why are you going after my sister?"

Chuck was furious now. "I'm not _going after_ your sister. She came to me. Why is it so hard to believe someone cares about me?"

"Cares?," Dan screamed, "Jenny doesn't care. She feels bad because you got dumped. By the way, you're here with Blair? Seriously? You come looking for Jenny and you show up with your ex. That's a nice way to show her _you _care."

"You know nothing," Blair spoke up. "That's not what was going on."

"Blair," Chuck said, "You don't have to defend me. He's being a good brother." And those were the words Dan never thought he'd hear from Chuck. "You know what?" He turned to Blair. "Let's go."

"Okay," she whispered. They started to walk out the door and she turned back. "Hey, Dan? Chuck does care." Then they were gone.

xxxxxxxxx

Jenny just got out of the shower and was sitting on her bed. There was a knock on the door and it opened. Serena walked in. "Hey," she whispered. "You want to talk about what happened tonight?"

"No," Jenny shook her head. "I don't. But" she sighed "I guess I need to." She took a deep breath and began. "I was supposed to go out with Chuck tonight. But when I was out earlier, I saw Blair and she wanted him back. I knew it. So I told him I couldn't do this and I ran out. I got in a cab with no idea where to go and ended up at that bar.

There was a guy who kept looking at me. He bought me a drink and asked me to dance. At first, I said no but then all I wanted was a good time and I started drinking more. I wasn't drunk, believe me. But we were dancing and he was…groping. I passed it off to the drinks and he wanted to see me again. But then Lily came in. It was nothing."

"Nothing?" Serena questioned when she finished. "Jenny, you met a strange guy in a bar! Who knows what could have happened?"

"Nothing did!"

"But how do you know that," she answered calmly. "If my mom hadn't come, something could have happened to you. At least if you're gonna be there, come with someone."

Jenny huffed. "You're one to talk about drinking, Serena." That was a low blow and she knew it.

"Okay, I deserve that," she said back, "But don't you think I might know if it's wrong then? He could have been anyone."

"I'm never gonna see him again, don't worry," was her reply.

There was a moment of silencelence between the two. Then Serena spoke up. "You did all this because of Chuck?" Jenny just nodded. "Take it from me, getting yourself drunk over a guy and then trying to hook up with another never ends well."

That gave her enough to think about.

xxxxxxxxx

It was 1 a.m. Jenny still couldn't sleep and her thoughts kept flashing between Chuck, the guy from the bar, and what Blair said that day. It was hard to think she was wrong to have left him in the hotel and it wasn't like something happened.

Her thoughts were interrupted by a cell phone buzzing. "Chuck" it said. She flipped open her phone and opened the text.

_Are you okay?_

She sighed. Why was he being sweet?

_Yes._

It vibrated a second later.

_What happened?_

_Nothing. I left you. Period._

_Were you drunk?_

_Is that your business?_

_You are my business. We're friends still._

_Are we?_

Nothing came back. Jenny was starting to think that response wasn't the best one. Then there was a light knock on the door. She got up from bed and out to the living room and answered it.

There stood Chuck.

"What are you doing here?" she asked him.

"This," he answered as he kissed her. It was one of those heart-stopping kisses that prove this is the person you're supposed to be with. Neither of them had time to catch their breath. Jenny instantly kissed him back, wrapping her arms around his neck and Chuck responded by placing his arms on her waist.

Both were panting and needing breath so she pulled away first and pushed him outside. "We can't do this, Chuck."

"Why," he asked her. "If this is about Blair, I told you -"

"No," she shook her head. "This isn't right. We're not right. There is too much baggage here for me and you to happen, okay?"

"No," he abruptly said, "That's not what this is about. I know how you feel and you know how I feel so what is the problem here? Are you letting everyone tell you how to feel?"

She couldn't believe what she was hearing. "No."

"Then what is this?"

"I told you," she said, "We aren't right for each other. Let's go back to whatever the hell we were, or if you don't want to, we'll be nothing to each other. But this can't work. Please, Chuck."

"I don't believe that," he said after a while. "You wanted this and now you're turning your back on it. Be honest. Is it Blair?"

"Yes and no," he excuses confused him once more. "You love Blair. I'm not going to step in and take something that's not even mine."

"Jenny, you're wrong," he whispered.

She huffed for the second time that night, "Really? Why is that?"

"Because I'm falling in love with you."


End file.
